2-carboxy-5-nitro diphenyl



Patented Aug.- 15, Q I p Z-CARBOXY-S-NITRO DIPHENYL William S. Jones and William BrakerQBrooklyn,

N. Y., assignors to E. R. Squibb & Sons, Brooklyn, N. Y., a Corporation of New York No Drawing. Application February 15, 1932 Serial No. 593,191

1 Claim.

This invention relates to 2 -ca-rboxy-5-nitro diphenyl. This compoundhas proved valuable particularly as an intermediate in the production of therapeutically active compounds.

5 The new compound is advantageously prepared by diazotizing 2-amino-5-nitro diphenyl, and then treating the diazotized product with a cyanide to form the nitrile which is 2-cyano-5-nit1'o diphenyl. The nitrile is next hydrolized to form l0 the desired carboxylic acid; The reaction is indicated by the following equation: a

The 2-amino-5-nitro diphenylwhich. is used as the starting material may be prepared by the method given in the Journal or the Chemical S0 ciety, vol. 2, 1928, page 2774, or preferably by hydrolysis of 5-nitro-2-para-to1uene sulfonamido diphenyl. Y a

25.0 grams of 2-amino-5-nitro diphenyl is dissolved in 24.0 cc. of hydrochloric acid (concen- 3O trated) contained in '75 cc. of water The solution is diazotized with 10.44 grams of sodium nitrite; the excess nitrite is destroyed by the additer.

tion of solid urea. This diazonium solution is addedover a period of about one-half hour to a solution of potassium copper cyanide kept at 90 C. This cyanide solution may be prepared by dissolving 50.0 grams of crystalline copper sulfate and 56.0 grams of potassium cyanide in sufiicient water to bring the total to 300 cc. The 1 reaction mixture is heated for six hours during which a crop of brown crystals form.- These crystals are filtered and washed free of inorganic mat The nitrile, viz. 2-cyano-5-nitro diphenyl thus obtained is recrystallized from alcohol. This compound has been found to have a melting point 5.2 grams of the nitrile is suspendedin asolution consisting of cc. of glacial acetic acid, 60 cc. of sulfuric acid and 50 cc. of water. The mix- 7 ture is refluxed for about eight hours. The resulting solution is diluted with an equal volume of wa- ,ter. The hydrolysis of the nitrile produces a crys- :5 ctalline substance which is filtered ofi. This compound is'washed with water and dried in vacuo.

It is the 2-carboxy-5-nitro diphenyl.

Our 'copending application, Serial No. 632,789

filed September 12, 1932, refers to a therapeuti- 'cally active compound prepared from 2-carboxy- 5-nitro diphenyl.

We claim: V 1 2-carboxy-5-nitro diphenyl.

WILLIAM S. JONES. WILLIAM BRAKER. 

